Building a business off of a bar napkin (Episode 44 ft. John Waldmann)

The hardest customer in software is usually the most underserved — and that's precisely the opportunity. John Waldmann is the Founder & CEO of Homebase, the team management platform now used by more than 150,000 small businesses. His path there ran through a teenage web design company called Angry Hippo, a tuxedo rental shop, BCG, and KKR — until two friends opened a restaurant and he saw firsthand how little technology existed for the people who needed it most. This conversation digs into the decisions behind the company: why he gave the product away free for four years when competitors charged per employee, why he turned down VC advice to go up-market, why he hired people with family-business backgrounds over traditional tech résumés, and how AI has made building at scale feel like the scrappy early days again. "They can't pay a lot of money. They shouldn't pay a lot of money, but their problems are no less acute." — John Waldmann